Triethylamine → 5-[(2-Chloroethyl)carbamoyloxy]-1,3-benzoxathiol-2-one

HRID 1702875Notes

Reaction equation

HRID 1702875 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[S:7][C:6]=2[CH:11]=1.[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].C(N(CC)CC)C>C(C(C)=O)C>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[S:7][C:6]=2[CH:11]=1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 1390671,3-Benzoxathiol-2-one, 5-hydroxy-

Product 1

HCID 130538395-[(2-Chloroethyl)carbamoyloxy]-1,3-benzoxathiol-2-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-hydroxy-1,3-benzoxathiol-2-one (14.0 grams) was mixed with 2-chloroethyl isocyanate (8.79 grams) in 170 milliliters of methyl ethyl ketone in the presence of 0.84 gram of triethylamine. The resulting mixture was heated at reflux temperature with stirring for 6 hours and 20 minutes. The solvent was then removed by evaporation in vacuo. The residue was recrystallized from carbon tetrachloride (containing a small amount of ethyl acetate). A subsequent recrystallization from toluene gave the purified product, 5-[(2-chloroethyl)carbamoyloxy]-1,3-benzoxathiol-2-one, as a white crystal line solid with a melting point of 105.5°-107.5° C. Elemental analysis calculated for C10H8ClNO4S (percent): carbon--43.88; hydrogen--2.95; nitrogen--5.12. Found: carbon--43.7; hydrogen--3.13; nitrogen--5.37.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature
  3. customThe solvent was then removed by evaporation in vacuo
  4. customThe residue was recrystallized from carbon tetrachloride (
  5. additioncontaining a small amount of ethyl acetate)
  6. customA subsequent recrystallization from toluene

Sources & evidence

ORD record
ord-bc0bea60603243508e244297564d82e4
Source dataset
uspto-grants-1982_09
Patent number
US04349685

Reaction notes

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